Location: Hidden Harbor, Sarasota
Do Not Show Listings
5309 HIDDEN HARBOR RD, SARASOTA, FL 34242
$4,500,000283 Days on yellowkey MLS ID: A4668550
Bed: 6 Bath: 6.0 Gar: 4 Liv Area Sq Ft: 6655 Built: 2007Monthly Fee: $247 Tax: $34,362 (2023)Community: Hidden HarborSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$34,362
Elementary School: None
High School: None
Tax Year: 2023
Middle School: None
Remarks: Majestic waterfront home nestled in one of Siesta Key's most exclusive neighborhoods. Prime waterfront location with direct access to the inter-coastal (no bridges) and features a 16,000 pound vertical lift and a jet ski lift. This Waterfront home features wraparound decks on multiple levels composed of Brazilian Ipe decking, wood ceilings, a private grill area with a dramatic view up the canal and a resort like swimming pool and spa featuring a rock waterfall and paver patio to fill your sun filled afternoons. Upon entering the home, you will see the amount of detail and craftsmanship that was put into this home. Hand-scraped wood flooring, coffered tongue-n-groove ceilings, huge baseboard and crown molding throughout. Expansive windows let the natural light in and an aquarium glass wall in the kitchen/family room overlooks your lower deck, swimming pool, spa and water view. The home has well over 6000 square feet of living area with the master suite occupying the first-floor level. This home affords 6 bedrooms, 5 full baths, 2 half baths, a private office with built-in cabinetry, 2 wet bars one on each level, 2 laundries with one on each level, a Sports room/ man cave with a built-in entertainment center. Upstairs has 4 bedrooms, two of which are suites, a second family room/playroom, theater/entertainment room which connects to your second level deck. The main level of the home incorporates your kitchen, family room, pantry, wet bar, dining room, private office, master suite and laundry. The kitchen features a huge walk-in pantry with entry door, a huge center island with a granite top, Subzero refrigerator, a Wolf 6 burner/griddle stove, a Wolf warming drawer, a Wolf microwave, 2 drawer Fisher Paykel dishwasher and a second Miele dishwasher for all your entertainment needs. Each level has a wet bar with the lower level having a subzero wine refrigerator and a drink refrigerator and the upstairs level has a Fisher Paykel dishwasher, an ice-maker, microwave, and a refrigerator. For the car enthusiast you have two 2 car garages with separate drives which provides additional parking as well. This spectacular home is hard to match, and you won't be disappointed. The home has an elevation of 15 feet and also has a home generator to provide comfort and a sense of security during any power outages that may occur. Schedule an appointment to see your future home!
Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)
Listing Agent: Brian Livesey (941-346-7454)
5215 HIDDEN HARBOR RD, SARASOTA, FL 34242
$7,675,00017 Days on yellowkey MLS ID: A4699085
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 4337 Built: 2026Monthly Fee: $247 Tax: $16,827 (2025)Community: Hidden HarborSpa: YesSingle Family
Taxes:$16,827
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Ready NOW. This exceptional waterfront estate by Dynan Construction, Sarasota's premier luxury builder, offers a rare opportunity to own a brand-new custom home without the wait. Renowned for impeccable craftsmanship, architectural integrity, and timeless coastal design, Dynan delivers a residence built to the Fortified Home Gold Standard, providing enhanced resilience against Florida's coastal elements while maintaining uncompromising luxury. Thoughtfully curated, every space reflects sophisticated design, elevated finishes, and enduring style. The gourmet kitchen is appointed with a premium Thermador appliance package, while Brizo plumbing fixtures are featured throughout the home, adding a refined level of quality and craftsmanship. This five bedroom single-story residence offers seven bathrooms - five full bathrooms, a dedicated pool bath, and an additional powder bath, creating a functional layout designed for both everyday living and effortless entertaining. Situated within the exclusive Hidden Harbor community—an intimate waterfront enclave known for its mature landscaping and lush, canopy-lined streets—the property enjoys a deep-water canal with direct access to Sarasota Bay and the Gulf of America. Designed to embrace Florida's indoor-outdoor lifestyle, expansive 10-foot sliding glass doors open to a resort-inspired outdoor living area complete with a custom pool and spa that is elevated to the finish floor of the home, covered pergola, and fully equipped outdoor kitchen. From sunrise cruises to sunset returns, enjoy the convenience of a private outdoor shower located just steps from the new dock and 10,000-pound boat lift. Every detail has been thoughtfully considered, from the seamless entertaining spaces to the carefully selected designer finishes throughout. Additional features include smart-home lighting controls, prewiring for security cameras and blinds, indoor/outdoor surround sound, and preparation for a future whole-house generator, providing convenience and peace of mind. Dual garage spaces—including a two-car garage and an additional one-car garage—offer the versatility to accommodate vehicles, water toys, bicycles, and storage with ease. Located just a short bike ride from the world-renowned Siesta Key Beach, this remarkable home combines luxury, durability, and an exceptional waterfront lifestyle with easy access to Sarasota's finest beaches, dining, shopping, and cultural attractions.
Listing is courtesy of: COASTAL RESERVE (941-586-7736)
Listing Agent: Cassandra Miller (941-586-7736)
5132 JUNGLE PLUM RD, SARASOTA, FL 34242
$5,685,000438 Days on yellowkey MLS ID: A4651663
REDUCED by $300,000 (5.0%) on 07/15/2026
Bed: 5 Bath: 6.0 Gar: 10 Liv Area Sq Ft: 6928 Built: 2008Monthly Fee: $247 Tax: $45,860 (2024)Community: Hidden HarborSpa: YesSingle Family
Taxes:$45,860
Tax Year: 2024
Remarks: Positioned along a deepwater canal in the private, tree-lined enclave of Hidden Harbor on Siesta Key, this remarkable estate captures the essence of timeless coastal architecture and elevated Florida living. With a design that transcends trends and nearly 7,000 square feet of thoughtfully curated interiors, the home embodies a sense of enduring sophistication, where natural materials, warm textures and elegant proportions create an atmosphere that is refined and welcoming. Just over a mile from the world-renowned sands of Siesta Key Beach, this is a home that celebrates the best of Sarasota’s lifestyle, a water connection, a celebration of indoor-outdoor living and architectural details that convey quiet luxury. Set on more than half an acre with 135 feet of water frontage, the residence opens with a stunning walnut-domed foyer, where soaring ceilings and floor-to-ceiling windows flood the space with light. Rich finishes—including Birdseye maple, tongue-and-groove cypress tray ceilings, and handcrafted millwork—are woven throughout the home, delivering a consistent sense of quality and character. The kitchen is a dream for chefs and entertainers alike, appointed with quartz countertops, a large center island, professional-grade appliances, a built-in espresso machine, and a walk-in butler’s pantry that seamlessly connects to formal and casual living areas. The owner’s suite is a private retreat, complete with a sitting room, dual walk-in closets, a spa-style bath with steam shower and a peaceful balcony overlooking the water. Each of the four guest suites offers its own en-suite bathroom and generous closet space, with three featuring walk-in closets and one boasting a built-in wall closet, ensuring privacy and comfort. Whether you need a quiet office, a vibrant game room or a cozy retreat, the bonus room, game room and loft offer the flexibility to suit your lifestyle. True to its coastal character, the home opens fully to expansive covered terraces designed for year-round enjoyment. Retractable screens, a wood-paneled ceiling, integrated fans, and ambient lighting create an outdoor living room atmosphere, complete with a fireplace and a full summer kitchen with built-in grill and bar seating. Beyond, the resort-style pool and raised spa are surrounded by tropical landscaping and natural stone decking, with multiple lounge areas designed for sun and shade. A custom fire pit anchors the space, offering a cozy, elegant setting for evening gatherings with water views. Water enthusiasts will appreciate the boat dock, built to accommodate a large vessel, complete with a boat lift. With quick access to the Intracoastal Waterway, the location is as functional as it is beautiful. Below, the expansive under-building garage offers room for more than 10 vehicles across five bays, plus a workshop, EV charging station and golf cart storage. A brand new whole-house generator was installed in June of 2025, creating peace of mind. Set on a quiet cul-de-sac just minutes from Sarasota’s best beaches, shopping, dining and cultural destinations, this rare offering is a seamless blend of timeless design, superior craftsmanship and the relaxed elegance of coastal Florida living.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
5179 HIDDEN HARBOR RD, SARASOTA, FL 34242
$7,950,000279 Days on yellowkey MLS ID: A4669099
INCREASED by $450,000 (6.0%) on 06/10/2026
Bed: 6 Bath: 7.5 Gar: 3 Liv Area Sq Ft: 4900 Built: 2026 Tax: $9,659 (2024)Community: Hidden HarborSpa: YesSingle Family
Taxes:$9,659
Remarks: Pre-Construction. To be built. Welcome to this newly imagined Siesta Key residence, a world curated for those with a sophisticated palate for modern architecture at the edge of the sea. Here, light dances across water and peers through your windows blending luxury, privacy and resort-style living within the exclusive enclave of Hidden Harbor. The journey begins as you approach this designer estate—a vision of coastal modernism, 4,900 square feet under air and meticulously crafted by TDI Coastal Homes, celebrated for precision, integrity, and elegance. Clean lines and natural textures blend with lush tropical surroundings, setting the stage for a life that lives like an endless retreat. The lower level invites you to linger outdoors surrounded by the scent of the saltwater breeze and the sounds of the cascading waters of the 65-foot infinity pool and spa. A covered living space blurs the line between home and horizon. A custom waterslide arcs playfully into the pool, while beyond, your private dock with a 20,000-pound lift awaits spontaneous voyages to Roberts Bay. Ascend by elevator or sculpted staircase to the heart of the home—spaces that feel both expansive and intimate. Walls of glass reveal shimmering water views, while the Meile appliance suite anchors a chef’s kitchen made for creating fine cuisine and lasting memories. Every detail and finish bears the signature of master craftsmanship. The home’s six bedrooms include two primary suites, each a retreat of its own with spa-inspired baths. Six full and three half baths offer both comfort and convenience for family and guests alike. A 700-square-foot bonus space stands ready to become whatever your imagination allows—a golf simulator, game lounge, or wellness studio. A three-car garage, new seawall, whole-home generator, and zero water intrusion during the 2024 storms provide unmatched peace of mind. As evening settles, the home transforms. Ambient lighting glows across the infinity edge and the hush of the bay replaces the day’s energy. You can almost hear the future stories unfolding here—laughter by the pool, sunrise swims, quiet coffee on the terrace. 5179 Hidden Harbor Road isn’t just a home; it’s a state of being—modern, effortless, and deeply connected to the water.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Rudy Dudon (941-234-3991)
1280 HIDDEN HARBOR WAY, SARASOTA, FL 34242
$8,500,00026 Days on yellowkey MLS ID: A4696603
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 5649 Built: 2002Monthly Fee: $333 Tax: $65,212 (2025)Community: Hidden HarborSpa: YesSingle Family
Taxes:$65,212
Remarks: Privately positioned on a tropical peninsula on Siesta Key in the coveted community of Hidden Harbor, this extraordinary bayfront estate captures sweeping views across Sarasota Bay, the Intracoastal Waterway and the downtown Sarasota skyline. Set on 0.62 acres with 125 feet of panoramic waterfront, the residence was masterfully built by luxury builder M. L. Collingwood and thoughtfully designed to celebrate both architectural craftsmanship and the beauty of its remarkable setting. A protected deep-water harbor, a private 50-foot dock and 20,000-pound lift create an exceptional opportunity for the serious boater, while the home’s privacy, scale and resort-style outdoor living make it equally ideal as a serene waterfront retreat. From the moment you arrive, custom mahogany doors, beveled glass transoms, lush landscaping and a gracious entry introduce the timeless character found throughout the residence. Inside, soaring ceilings, generous room proportions and walls of glass frame magnificent water views from many of the principal living areas. Rich architectural details include coffered and tray ceilings, bentwood arches, crown molding, custom millwork and travertine inset flooring. The formal living and dining rooms flow beautifully for entertaining and are complemented by a fully outfitted cherrywood-paneled bar and wine room. The executive office and library are a showpiece, featuring cherrywood paneling, an 18-foot coffered ceiling and a spiral staircase leading to upper bookshelves. The well-appointed island kitchen offers Wood-Mode cabinetry, quartzite countertops, stainless steel appliances, paneled Sub-Zero refrigeration, a Viking six-burner gas range, dual ovens, a walk-in pantry and a spacious breakfast bar. Open to the bayfront breakfast and gathering rooms, the space features an electric fireplace, adding warmth and ambiance, and connects effortlessly to the outdoor living areas. The primary suite is a private waterfront sanctuary with a bayfront sitting room and a generous bath with dual vanities, a two-person shower, a soaking tub and private water closets. Two additional guest suites are privately positioned in their own wing on the main level, along with a powder bath and laundry room. Upstairs, a fourth bedroom or game room includes a full bath, walk-in closet and private western balcony overlooking the harbor, ideal for taking in evening sunsets. Designed for relaxed Florida living, the expansive lanai features a heated saltwater infinity-edge pool, travertine decking and a shaded outdoor living space with custom ceiling detail, creating an inviting setting for alfresco dining and waterfront entertaining. Frequent dolphin and manatee sightings add to the magic of this rare waterfront setting. Additional features include a side-entry three-car garage, a paver drive and walkways, landscape lighting, a walk-in attic and abundant storage. Hidden Harbor is one of Siesta Key’s most treasured boating communities, offering exceptional privacy just one mile from the powdery white sands of Siesta Beach and close to Siesta Village’s dining, shopping and island charm. Mainland Sarasota’s cultural venues, restaurants, shopping, medical facilities and schools, including nationally acclaimed Pine View School, are also within easy reach.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Judie Berger (941-928-3424)
5303 HIDDEN HARBOR RD, SARASOTA, FL 34242
$2,650,000156 Days on yellowkey MLS ID: N6143036
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 3201 Built: 1971Monthly Fee: $333 Tax: $24,081 (2025)Community: Hidden HarborSpa: NoSingle Family
Taxes:$24,081
Remarks: Now is your opportunity to own this waterfront tropical oasis on Siesta Key in the highly sought after exclusive community of Hidden Harbor. Comprised of just 36 homes, Hidden Harbor located on the North end of Siesta Key, is one of the most unique developments in Sarasota with its tropical landscaping reminiscent of old Florida. Most known for its waterfront lots and brick paver streets shaded by a magnificent canopy of lush greenery. This home has been beautifully reimagined to showcase its contemporary design and is situated on over half acre lot enjoying 119’ of deep-water canal front, making this a boater’s dream. The dock spans almost 40 feet and features a 10,000lb boat lift (installed in 2020) and has both electric and water supplies. No bridges to obstruct your journey out to Roberts Bay, which is just a turn of a corner away. The home features a new metal roof (2023), 4 new HVAC units that includes a garage unit (2024), and new hurricane impact sliders and windows (2021). On the inside you will find a floor plan that is flooded with natural light thanks to large sliders and tall architectural style windows that truly bring the Florida landscape inside. The first floor has all new luxury flooring and woodwork, including new solid core doors. The kitchen was recently renovated with European style cabinetry, stone counters, and a luxury Fisher & Paykel appliance package including range hood and induction cooktop. The two light-filled bedrooms on the East side of the home both feature access to outdoor spaces and walk-in closets. The shared bathroom, which also acts as a pool bath with its door to the outside, was renovated with a new seamless glass shower, European style vanity with LED mirror, and all new fixtures and hardware. Throughout the home, you will find restored original fixtures keeping with the home’s integrity. The primary suite dominates the second floor with a loft area, a light filled bedroom that enjoys the cross breeze when both walls of sliding windows are open, and a custom installed closet. There is an updated en-suite bathroom with another seamless glass shower and floating vanity with new upgraded fixtures. Outside the yard is truly a Florida paradise with fire pit area, stunning tropical landscaping with professionally installed low voltage lighting system, pest control misting system, and an impressive heated pool that was resurfaced and upgraded with a travertine deck. This property offers extreme privacy, architectural character and significance, and water views, all within one of the most unique neighborhoods on Siesta Key. The Hidden Harbor canal offers deep water for your boat or sailboat. Enjoy true island life, whether you find yourself relaxing by your pool, boating, fishing, kayaking, and even paddle-boarding all from your property. There is a natural seawall of mangroves, and the riprap was installed by the reputable Duncan Seawall. The world-famous Siesta Key Beach is just a short 1.5-mile bike ride, golf cart ride, or leisurely walk away. Enjoy local restaurants, boutiques, and live music at the island's lively Siesta Village. Close to the mainland and downtown Sarasota, this is a prime location for island living. If you are looking for your own piece of paradise, and a property that is truly unique, set up a private tour today!
Listing is courtesy of: COLDWELL BANKER REALTY (941-493-1000)
Listing Agent: Walter Shepherd (941-445-2455)
5155 HIDDEN HARBOR RD, SARASOTA, FL 34242
$1,995,000184 Days on yellowkey MLS ID: G5107159
2 Days Off yellowkey (back on 6/10/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2233 Built: 1973Monthly Fee: $332 Tax: $7,806 (2025)Community: Hidden HarborSpa: NoSingle Family
Taxes:$7,806
Remarks: Nearly 200 feet of deep-water frontage in the prestigious Hidden Harbor enclave of Siesta Key—no bridges, quick access to Roberts Bay and the Gulf of America. Move-in ready and never flooded. Enjoy island living in this private waterfront setting surrounded by multi-million dollar estates. Lush, canopy-lined brick paver streets, wide water views, no through streets, and excellent boating access. The home has been thoughtfully renovated with an emphasis on functionality and storage, featuring an updated kitchen, modernized bathrooms, tile flooring throughout, recessed lighting, impact-rated windows and sliders, landscape lighting, a dedicated well with irrigation system, and a heated saltwater pool. Bike to the award-winning Siesta Key Beach, dine and shop in Siesta Village, kayak from your dock to nearby mangrove tunnels, or enjoy the convenience of downtown Sarasota less than seven miles away. A rare waterfront home offering immediate enjoyment and long-term upside in a neighborhood experiencing significant luxury redevelopment.
Listing is courtesy of: LIST NOW REALTY, LLC (352-385-7636)
Listing Agent: Matt Buttner (352-385-7636)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.